4-Toluenesulfonyl chloride → HCID 59026670, compound

HRID 606139Notes

Reaction equation

HRID 606139 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][C:19]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][N:20]=2)[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[NH4+:53]>>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][C:19]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][N:20]=2)[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:53])[C:8]=2[N:17]=1)[CH3:2]

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 67041249HCID 67041249, compound

Product 1

HCID 59026670HCID 59026670, compound

Procedure

The methods described in Part I of Example 35 were used to treat 2-(ethoxymethyl)-1-[(5-phenylisoxazol-3-yl)methyl]-1H-imidazo[4,5-c]quinoline (0.650 g, 1.69 mmol) with mCPBA (0.455 g of 77% pure material, 2.0 mmol) followed by p-toluenesulfonyl chloride (0.355 g, 1.86 mmol) and concentrated ammonium hydroxide (15 mL) and purify the final product to provide 0.38 g of 2-(ethoxymethyl)-1-[(5-phenylisoxazol-3-yl)methyl]-1H-imidazo[4,5-c]quinolin-4-amine as a tan crystalline solid, mp 221-223° C.

Workup

  1. custompurify the final product

Sources & evidence

ORD record
ord-2b42a96c3f4e411ca9abe0fd71bc81d8
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

Loading…